On Monday’s “Morning Joe” on MSNBC, former Michael Leiter, the former director of the U.S. National Counterterrorism Center (NCTC) for both Presidents George W. Bush and Barack Obama reacted to last weekend’s hostage swap, which U.S. Army Sgt. Bowe Bergdahl was exchanged for five Taliban that were being held at Guantanamo Bay.

Weekly Standard editor Bill Kristol, a guest on “Morning Joe,” asked Leiter if perhaps it would have been more appropriate for the Obama administration to have negotiated his release once this conflict had ran its course. Leiter said that would be ideal, but not always possible. He did, however, call this “problematic” in that comes off as a “big win” for U.S. adversaries in Afghanistan.

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“I think that’s right,” Leiter said. “But it’s also hard to choreograph these things all that perfectly. If the opportunity was there now, I think that’s why the administration took it. And to say let’s keep winding things down until 2016 and then get them back — there’s just no guarantee of that. But I’m not going to disagree with you entirely. I do think that these five who were really far on the far end of the spectrum of bad guys in Guantanamo — this is really problematic. For the long-term, this is going to strengthen the Taliban. Our hand is obviously weakening there. And I think them going back, listen it’s going to turn the tide in but it is strengthening them and Afghanistan. I think the tide has probably already turned. But it is strengthening them and it is a big win for them.”